1-Bromo-2-nitrobenzene → HCID 87210606, compound

HRID 2167317Notes

Reaction equation

HRID 2167317 reaction equation
[C:1]1([C:11]2C3C([C:18]([C:28]4[C:37]5C(=CC=CC=5)C=CC=4)=[C:19]4[C:24]=2[CH:23]=[C:22](B(O)O)[CH:21]=[CH:20]4)=CC=CC=3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[N+:45]([O-:47])=[O:46].C([O-])([O-])=O.[K+].[K+].O1[CH2:59][CH2:58]OCC1>C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:45]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[C:11]1[CH:1]=[CH:2][C:3]2[C:23](=[C:22]([C:59]3[CH:58]=[CH:9][C:10]4[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=4)[CH:11]=3)[C:21]3[C:20]([C:4]=2[C:5]2[CH:10]=[CH:9][C:8]4[C:7](=[CH:28][CH:18]=[CH:19][CH:20]=4)[CH:6]=2)=[CH:19][CH:18]=[CH:28][CH:37]=3)[CH:24]=1)([O-:47])=[O:46]

Participants

8

Reactant 4

HCID 113411-Bromo-2-nitrobenzeneHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 23160234[9,10-Di(naphthalen-1-yl)anthracen-2-yl]boronic acid

Product 1

HCID 87210606HCID 87210606, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

10 g (21.1 mmol) of 9,10-dinaphthylanthracene-2-boronic acid, 10.64 g (52.7 mmol) of bromonitrobenzene, 1.21 g (0.05 mmol) of Pd(PPh3)4, and 11.65 g (84.3 mmol) of K2CO3 were diluted with 100 ml of dioxane, 100 ml of THF, and 30 ml of H2O, and then, the mixture was refluxed while heating. After 12 hours, a solvent was removed and the resultant mixture was extracted using MC and washed with a saturated NaCl solution. Then, an organic layer was dried and condensed over MgSO4, and the obtained product was purified by column chromatography (MC/Hex=1/5), thereby producing 2-(2-nitrophenyl)-9,10-di(2-naphthyl)anthracene that was yellow solid (8.4 g, 73%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewhile heating
  3. customa solvent was removed
  4. extractionthe resultant mixture was extracted
  5. washwashed with a saturated NaCl solution
  6. customThen, an organic layer was dried
  7. customcondensed over MgSO4
  8. customthe obtained product was purified by column chromatography (MC/Hex=1/5)

Sources & evidence

ORD record
ord-8b87d5156a3a4774a23e44d227760b5e
Source dataset
uspto-grants-2015_06
Patent number
US09045419B2

Reaction notes

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